Chemical Properties
Pronamide is a colorless crystalline solid or
powder.
Chemical Properties
White Solid
Uses
Selective pre-emergence herbicide.
Uses
Preemergence or postemergence herbicide used to control many perennial and annual
grasses and broad-leaved weeds in ornamental trees and shrubs, forestry, fruits and vegetables
Definition
ChEBI: A member of the class of benzamides resulting from the formal condensation of the carboxy group of 3,5-dichlorobenzoic acid with the amino group of 2-methylbut-3-yn-2-amine. It is used as a systemic post-emergent herbicide for the control grass and broadle
f weeds in a wide range of in a wide variety of fruit and root crops.
General Description
White solid. Used as a selective herbicide.
Reactivity Profile
3,5-DICHLORO-N-(1,1-DIMETHYL-2-PROPYNYL)BENZAMIDE is a chlorinated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Agricultural Uses
Herbicide: Pronamide is a selective herbicide used either before weeds emerge (pre-emergence), and/or after weeds come up (post-emergence). It controls a wide range of annual and perennial grasses, as well as certain annual broadleaf weeds. It is used primarily on lettuce and alfalfa crops, as well as on blueberries, ornamentals, fruit trees, forage legumes, and on pastures and rangelands. Pronamide is usually incorporated into the soil by cultivation, irrigation, or rain immediately following application. It is available in wettable powder and granular formulations. Registered for use in the U.S. and EU countries. A U.S. EPA restricted Use Pesticide (RUP).
Trade name
BENZAMIDE®; CAMPBELL'S RAPIER®; CLANEX®; KERB®; KERB 50 W®; KERB® PROPYZAMIDE 50; RH-315 RAPIER®; RONAMID®
Synthesis
As shown in Figure 3, 2-methyl-3-butyn-2-amine, triethylamine and dichloromethane were sequentially added to the reactor, stirred and cooled to 0 °C. 3,5-dichlorobenzoyl chloride was added dropwise at a temperature controlled below 15 °C. After the addition was completed, the reaction mixture was kept at 0°C to continue the reaction for 10 hours, followed by warming up to room temperature for 2 hours. After completion of the reaction, the product was separated by centrifugation and dried to afford 3,5-dichloro-N-(2-methylbut-3-yn-2-yl)benzamide (93% yield, 99% purity). The mass spectral (MS, m/z 255) and 1H NMR (δ 6.54, 6.74, 6.86) data of the obtained compounds were in agreement with the reference standards, confirming the successful synthesis of the target compounds.
Potential Exposure
A potential danger to those involved
in the manufacture, formulation and application of this
selective herbicide.
Environmental Fate
Biological. In the presence of suspended natural populations from unpolluted aquatic
systems, the second-order microbial transformation rate constant determined in the laboratory was reported to be 5 × 10–14 L/organisms-hour (Steen, 1991).
Soil. The major soil metabolite is 2-(3,5-dichlorophenyl)-4,4-dimethyl-5-methyleneoxazoline. The half-life in soil is approximately 30 days at 25°C (Hartley and Kidd, 1987).
Residual activity in soil is limited to approximately 2–6 months (Hartley and Kidd, 1987).
Chemical/Physical. Emits toxic fumes of nitrogen oxides and chlorine when heated
to decomposition (Sax and Lewis, 1987).
Propyzamide is hydrolyzed to 3,5-dichlorobenzoate by refluxing under strongly acidic
conditions (Humburg et al., 1989).
Shipping
UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous haz-
ardous material, Technical Name Required.
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explo-
sions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Compounds of the car-
boxyl group react with all bases, both inorganic and
organic (i.e., amines) releasing substantial heat, water and a
salt that may be harmful. Incompatible with arsenic com-
pounds (releases hydrogen cyanide gas), diazo compounds,
dithiocarbamates, isocyanates, mercaptans, nitrides, and
sulfides (releasing heat, toxic and possibly flammable
gases), thiosulfates and dithionites (releasing hydrogen
sulfate and oxides of sulfur).
Waste Disposal
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform with EPA regulations govern-
ing storage, transportation, treatment, and waste disposal.
In accordance with 40CFR165, follow recommendations
for the disposal of pesticides and pesticide containers. Must
be disposed properly by following package label directions
or by contacting your local or federal environmental control
agency, or by contacting your regional EPA office.
References
[1] Patent: CN107903181, 2018, A. Location in patent: Paragraph 0011-0012; 0044-0046; 0051
[2] Patent: CN107540566, 2018, A. Location in patent: Paragraph 0017; 00180024
[3] Journal of Organic Chemistry, 2018,
